U.S. patent number 10,112,959 [Application Number 15/529,046] was granted by the patent office on 2018-10-30 for metal complex and color conversion film comprising same.
This patent grant is currently assigned to LG CHEM, LTD.. The grantee listed for this patent is LG CHEM, LTD.. Invention is credited to Minyoung Kang, Kichul Koo, Duy Hieu Le, Hoyong Lee.
United States Patent |
10,112,959 |
Lee , et al. |
October 30, 2018 |
Metal complex and color conversion film comprising same
Abstract
The present disclosure relates to a novel compound, a color
conversion film, a backlight unit and a display device comprising
the same.
Inventors: |
Lee; Hoyong (Daejeon,
KR), Koo; Kichul (Daejeon, KR), Kang;
Minyoung (Daejeon, KR), Le; Duy Hieu (Daejeon,
KR) |
Applicant: |
Name |
City |
State |
Country |
Type |
LG CHEM, LTD. |
Seoul |
N/A |
KR |
|
|
Assignee: |
LG CHEM, LTD. (Seoul,
KR)
|
Family
ID: |
56284524 |
Appl.
No.: |
15/529,046 |
Filed: |
October 26, 2015 |
PCT
Filed: |
October 26, 2015 |
PCT No.: |
PCT/KR2015/011332 |
371(c)(1),(2),(4) Date: |
May 23, 2017 |
PCT
Pub. No.: |
WO2016/108411 |
PCT
Pub. Date: |
July 07, 2016 |
Prior Publication Data
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|
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Document
Identifier |
Publication Date |
|
US 20170260212 A1 |
Sep 14, 2017 |
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Foreign Application Priority Data
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|
|
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Dec 29, 2014 [KR] |
|
|
10-2014-0192221 |
|
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C07F
5/022 (20130101); C08K 5/55 (20130101); F21K
9/64 (20160801); C07F 5/02 (20130101) |
Current International
Class: |
C07F
5/02 (20060101); C08K 5/55 (20060101); F21K
9/64 (20160101); F21V 9/30 (20180101) |
Field of
Search: |
;524/105 |
References Cited
[Referenced By]
U.S. Patent Documents
Foreign Patent Documents
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|
|
2005-154534 |
|
Jun 2005 |
|
JP |
|
201018788 |
|
Jan 2010 |
|
JP |
|
2013-105665 |
|
May 2013 |
|
JP |
|
2009/116456 |
|
Sep 2009 |
|
WO |
|
WO-2009116456 |
|
Sep 2009 |
|
WO |
|
2010/032453 |
|
Mar 2010 |
|
WO |
|
2014/182704 |
|
Nov 2014 |
|
WO |
|
Other References
Jillian G. Baker et al., "Synthesis and Characterization of
High-Affinity 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene-Labeled
Fluorescent Ligands for Human -Adrenoceptors", Journal of Medicinal
Chemistry, vol. 54, Issue 19, Aug. 29, 2011, pp. 6874-6887. cited
by applicant.
|
Primary Examiner: Bernshteyn; Michael
Attorney, Agent or Firm: Dentons US LLP
Claims
The invention claimed is:
1. A compound of the following Chemical Formula 1: ##STR00038##
wherein, in Chemical Formula 1, at least one of R.sub.1 to R.sub.5
is selected from among the following structural formulae;
##STR00039## R.sub.6 is hydrogen; a nitrile group; a substituted or
unsubstituted alkyl group; a substituted or unsubstituted
cycloalkyl group; a substituted or unsubstituted alkoxy group; a
substituted or unsubstituted aryl group; a substituted or
unsubstituted alkylaryl group; or a substituted or unsubstituted
aromatic or aliphatic heterocyclic group; X.sub.1 and X.sub.2 are
the same as or different from each other, and each independently F;
a nitrile group; a substituted or unsubstituted alkynyl group; a
substituted or unsubstituted alkyl group; a substituted or
unsubstituted alkoxy group; a substituted or unsubstituted aryloxy
group; a substituted or unsubstituted arylalkoxy group; a
substituted or unsubstituted aryl group; or a substituted or
unsubstituted aromatic or aliphatic heterocyclic group, or bond to
each other to form an aromatic or aliphatic ring; X.sub.3 is a
halogen group; a nitrile group; a carbonyl group; an ester group;
an amide group; a sulfonate group; a substituted or unsubstituted
alkyl group; a fluoroalkyl group; a substituted or unsubstituted
cycloalkyl group; a substituted or unsubstituted alkoxy group; a
substituted or unsubstituted alkylsulfoxy group; a substituted or
unsubstituted silyl group; a substituted or unsubstituted phosphine
oxide group; or a substituted or unsubstituted alkylaryl group;
Y.sub.1 is CR.sub.101 or N, Y.sub.2 is CR.sub.102 or N, Y.sub.3 is
CR.sub.103 or N and Y.sub.4 is CR.sub.104 or N; and groups of
R.sub.1 to R.sub.5 that are not the above-mentioned structural
formulae, R.sub.8 to R.sub.13 and R.sub.101 to R.sub.104 are the
same as or different from each other, and each independently
hydrogen; deuterium; a halogen group; a nitrile group; a nitro
group; a carbonyl group; an ester group; an imide group; an amide
group; a sulfonate group; a substituted or unsubstituted alkyl
group; a substituted or unsubstituted cycloalkyl group; a
substituted or unsubstituted alkoxy group; a substituted or
unsubstituted aryloxy group; a substituted or unsubstituted
alkylthioxy group; a substituted or unsubstituted arylthioxy group;
a substituted or unsubstituted alkylsulfoxy group; a substituted or
unsubstituted arylsulfoxy group; a substituted or unsubstituted
alkenyl group; a substituted or unsubstituted silyl group; a
substituted or unsubstituted boron group; a substituted or
unsubstituted arylphosphine group; a substituted or unsubstituted
phosphine oxide group; a substituted or unsubstituted arylalkyl
group; a substituted or unsubstituted alkylaryl group; a
substituted or unsubstituted aryl group; or a substituted or
unsubstituted aromatic or aliphatic heterocyclic group, and R.sub.9
and R.sub.10 bond to each other to form an aliphatic or aromatic
ring, and R.sub.12 and R.sub.13 bond to each other to form an
aliphatic or aromatic ring.
2. The compound of claim 1, wherein R.sub.1 to R.sub.4 are the same
as or different from each other, and each independently hydrogen,
deuterium, a substituted or unsubstituted alkyl group, a
substituted or unsubstituted alkylaryl group, a substituted or
unsubstituted arylalkyl group, a substituted or unsubstituted aryl
group, or one of the following structural formulae: ##STR00040##
wherein definitions of R.sub.8 to R.sub.13 are the same as those
described above.
3. The compound of claim 1, wherein R.sub.5 is hydrogen, deuterium,
or one of the following structural formulae: ##STR00041## wherein
definitions of R.sub.8 to R.sub.13 are the same as those described
above.
4. The compound of claim 1, wherein Y.sub.1 to Y.sub.4 are the same
as or different from each other, and each independently CH, CF or
N.
5. The compound of claim 1, wherein the compound of Chemical
Formula 1 has a maximum light emission peak present in 520 nm to
550 nm in a film state.
6. The compound of claim 1, wherein the compound of Chemical
Formula 1 has a maximum light emission peak present in 520 nm to
550 nm in a film state, and a half-width of the light emission peak
is 50 nm or less.
7. The compound of claim 1, wherein the compound of Chemical
Formula 1 has a maximum light emission peak present in 610 nm to
650 nm in a film state.
8. The compound of claim 1, wherein the compound of Chemical
Formula 1 has a maximum light emission peak present in 610 nm to
650 nm in a film state, and a half-width of the light emission peak
is 60 nm or less.
9. The compound of claim 1, wherein the compound of Chemical
Formula 1 has quantum efficiency of 0.9 or more.
10. The compound of claim 1, wherein Chemical Formula 1 is selected
from among the following structural formulae: ##STR00042##
##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047##
##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052##
##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057##
##STR00058## ##STR00059## ##STR00060## ##STR00061##
11. A color conversion film comprising: a resin matrix; and the
compound of Chemical Formula 1 of claim 1 dispersed into the resin
matrix.
12. A backlight unit comprising the color conversion film of claim
11.
13. A display device comprising the backlight unit of claim 12.
Description
TECHNICAL FIELD
This application is a National Stage Application of International
Application No. PCT/KR2015/011332 filed on Oct. 26, 2015, which
claims the benefit of Korean Patent Application No. 10-
2014-0192221 filed on Dec. 29, 2014, all of which are hereby
incorporated by reference in their entirety for all purposes as if
fully set forth herein.
The present application relates to a novel metal complex and a
color conversion film comprising the same. In addition, the present
application relates to a backlight unit and a display device
including the color conversion film.
BACKGROUND ART
Existing light emitting diodes (LED) are obtained either by mixing
a green phosphorescent substance and a red phosphorescent substance
to a blue light emitting diode, or mixing a yellow phosphorescent
substance and a blue-green phosphorescent substance to a UV-light
emission light emitting diode. However, such a method is difficult
to control colors and accordingly, color rendering is not
favorable. As a result, Color Gamut is inferior.
In order to overcome such Color Gamut decline, and reduce
production costs, a method obtaining green and red by filming
quantum dots and binding the result to a blue LED has been recently
tried. However, cadmium series quantum dots have safety problems,
and other quantum dots have significantly lower efficiency than
cadmium series. In addition, quantum dots have a disadvantage in
that they have inferior stability for oxygen and water, and when
aggregated, the performance significantly declines. Furthermore,
unit production costs are high since maintaining constant sizes is
difficult when quantum dots are produced.
PRIOR ART DOCUMENTS
Patent Documents
Korean Patent Application Laid-Open Publication No.
2000-0011622.
DISCLOSURE
Technical Problem
The present application provides a novel metal complex and a color
conversion film comprising the same. In addition, the present
application provides a backlight unit and a display device
including the color conversion film.
Technical Solution
One embodiment of the present application provides a compound of
the following Chemical Formula 1.
##STR00001##
In Chemical Formula 1,
at least one of R.sub.1 to R.sub.5 is selected from among the
following structural formulae,
##STR00002##
R.sub.6 is hydrogen; a nitrile group; a substituted or
unsubstituted alkyl group; a substituted or unsubstituted
cycloalkyl group; a substituted or unsubstituted alkoxy group; a
substituted or unsubstituted aryl group; a substituted or
unsubstituted alkylaryl group; or a substituted or unsubstituted
aromatic or aliphatic heterocyclic group,
X.sub.1 and X.sub.2 are the same as or different from each other,
and each independently F; a nitrile group; a substituted or
unsubstituted alkynyl group; a substituted or unsubstituted alkyl
group; a substituted or unsubstituted alkoxy group; a substituted
or unsubstituted aryloxy group; a substituted or unsubstituted
arylalkoxy group; a substituted or unsubstituted aryl group; or a
substituted or unsubstituted aromatic or aliphatic heterocyclic
group, or bond to each other to form an aromatic or aliphatic
ring,
X.sub.3 is a halogen group; a nitrile group; a carbonyl group; an
ester group; an amide group; a sulfonate group; a substituted or
unsubstituted alkyl group; a fluoroalkyl group; a substituted or
unsubstituted cycloalkyl group; a substituted or unsubstituted
alkoxy group; a substituted or unsubstituted alkylsulfoxy group; a
substituted or unsubstituted silyl group; a substituted or
unsubstituted phosphine oxide group; or a substituted or
unsubstituted alkylaryl group,
Y.sub.1 is CR.sub.101 or N, Y.sub.2 is CR.sub.102 or N, Y.sub.3 is
CR.sub.103 or N and Y.sub.4 is CR.sub.104 or N, and
groups of R.sub.1 to R.sub.5 that are not the above-mentioned
structural formulae, R.sub.8 to R.sub.13 and R.sub.101 to R.sub.104
are the same as or different from each other, and each
independently hydrogen; deuterium; a halogen group; a nitrile
group; a nitro group; a carbonyl group; an ester group; an imide
group; an amide group; a sulfonate group; a substituted or
unsubstituted alkyl group; a substituted or unsubstituted
cycloalkyl group; a substituted or unsubstituted alkoxy group; a
substituted or unsubstituted aryloxy group; a substituted or
unsubstituted alkylthioxy group; a substituted or unsubstituted
arylthioxy group; a substituted or unsubstituted alkylsulfoxy
group; a substituted or unsubstituted arylsulfoxy group; a
substituted or unsubstituted alkenyl group; a substituted or
unsubstituted silyl group; a substituted or unsubstituted boron
group; a substituted or unsubstituted arylphosphine group; a
substituted or unsubstituted phosphine oxide group; a substituted
or unsubstituted arylalkyl group; a substituted or unsubstituted
alkylaryl group; a substituted or unsubstituted aryl group; or a
substituted or unsubstituted aromatic or aliphatic heterocyclic
group, and R.sub.9 and R.sub.10 may bond to each other to form an
aliphatic or aromatic ring, and R.sub.12 and R.sub.13 may bond to
each other to form an aliphatic or aromatic ring.
Another embodiment of the present application provides a color
conversion film including a resin matrix; and the compound of
Chemical Formula 1 dispersed into the resin matrix.
Still another embodiment of the present application provides a
backlight unit including the color conversion film.
Yet still another embodiment of the present application provides a
display device including the backlight unit.
Advantageous Effects
A metal complex described in the present specification has a
substituent (X.sub.3) at the ortho position, and provides a green
fluorescent substance having a small half-width and thereby having
high efficiency. When the metal complex does not have a substituent
(X.sub.3) at the ortho position, a light emission wavelength is
red-shifted, which is not suitable as a green fluorescent
substance, and causes a problem of an efficiency decrease due to a
half-width increase. In addition, in the metal complex described in
the present specification, an electron-withdrawing group is
introduced to at least one of R.sub.1 to R.sub.5, and therefore,
the metal complex lowers oxidation potential and thereby lowers
reactivity with singlet oxygen, and as a result, light stability in
a color conversion film that does not use a barrier film
significantly increases. Accordingly, by using the metal complex
described in the present specification as a fluorescent material of
a color conversion film, a color conversion film having excellent
luminance and Color Gamut, and having a simple manufacturing
process and low unit manufacturing costs by not using a barrier
film can be provided.
DESCRIPTION OF DRAWINGS
FIG. 1 is a mimetic diagram using a color conversion film according
to one embodiment of the present application to a backlight.
FIG. 2 shows light emission spectra (toluene 1.times.10.sup.-5 M)
of Compound 1 (dotted line) and Compound 2 (straight line).
FIGS. 3, 4 and 6 show changes in UV-vis spectra of Compound 1,
Compound 3 and Compound 1-40 by time under blue light,
respectively.
FIG. 5 shows absorbance variation in maximum absorption wavelengths
of Compound 1 and Compound 3 by time.
FIG. 7 shows absorbance variation in maximum absorption wavelengths
of Compound 1 and Compound 1-40 by time.
FIG. 8 shows intensity variation in green fluorescence of a color
conversion film prepared using Compound 1, Compound 3, Compound
1-9, Compound 1-40, Compound 1-41 or Compound 1-43 by time under
the driving of a blue backlight.
MODE FOR DISCLOSURE
One embodiment of the present application provides a compound of
the following Chemical Formula 1:
##STR00003##
In Chemical Formula 1,
at least one of R.sub.1 to R.sub.5 is selected from among the
following structural formulae,
##STR00004##
R.sub.6 is hydrogen; a nitrile group; a substituted or
unsubstituted alkyl group; a substituted or unsubstituted
cycloalkyl group; a substituted or unsubstituted alkoxy group; a
substituted or unsubstituted aryl group; a substituted or
unsubstituted alkylaryl group; or a substituted or unsubstituted
aromatic or aliphatic heterocyclic group,
X.sub.1 and X.sub.2 are the same as or different from each other,
and each independently F; a nitrile group; a substituted or
unsubstituted alkynyl group; a substituted or unsubstituted alkyl
group; a substituted or unsubstituted alkoxy group; a substituted
or unsubstituted aryloxy group; a substituted or unsubstituted
arylalkoxy group; a substituted or unsubstituted aryl group; or a
substituted or unsubstituted aromatic or aliphatic heterocyclic
group, or bond to each other to form an aromatic or aliphatic
ring,
X.sub.3 is a halogen group; a nitrile group; a carbonyl group; an
ester group; an amide group; a sulfonate group; a substituted or
unsubstituted alkyl group; a fluoroalkyl group; a substituted or
unsubstituted cycloalkyl group; a substituted or unsubstituted
alkoxy group; a substituted or unsubstituted alkylsulfoxy group; a
substituted or unsubstituted silyl group; a substituted or
unsubstituted phosphine oxide group; or a substituted or
unsubstituted alkylaryl group,
Y.sub.1 is CR.sub.101 or N, Y.sub.2 is CR.sub.102 or N, Y.sub.3 is
CR.sub.103 or N and Y.sub.4 is CR.sub.104 or N, and
groups of R.sub.1 to R.sub.5 that are not the above-mentioned
structural formulae, R.sub.8 to R.sub.13 and R.sub.101 to R.sub.104
are the same as or different from each other, and each
independently hydrogen; deuterium; a halogen group; a nitrile
group; a nitro group; a carbonyl group; an ester group; an imide
group; an amide group; a sulfonate group; a substituted or
unsubstituted alkyl group; a substituted or unsubstituted
cycloalkyl group; a substituted or unsubstituted alkoxy group; a
substituted or unsubstituted aryloxy group; a substituted or
unsubstituted alkylthioxy group; a substituted or unsubstituted
arylthioxy group; a substituted or unsubstituted alkylsulfoxy
group; a substituted or unsubstituted arylsulfoxy group; a
substituted or unsubstituted alkenyl group; a substituted or
unsubstituted silyl group; a substituted or unsubstituted boron
group; a substituted or unsubstituted arylphosphine group; a
substituted or unsubstituted phosphine oxide group; a substituted
or unsubstituted arylalkyl group; a substituted or unsubstituted
alkylaryl group; a substituted or unsubstituted aryl group; or a
substituted or unsubstituted aromatic or aliphatic heterocyclic
group, and R.sub.9 and R.sub.10 may bond to each other to form an
aliphatic or aromatic ring, and R.sub.12 and R.sub.13 may bond to
each other to form an aliphatic or aromatic ring.
The compound of Chemical Formula 1 has a substituent (X.sub.3) at
the pyrromethane metal complex core, and provides a fluorescent
substance having a small half-width and thereby having high
efficiency. In addition, in the compound of Chemical Formula 1, a
specific type of an electron-withdrawing group is introduced to at
least one of R.sub.1 to R.sub.5 and therefore, the compound of
Chemical Formula 1 lowers oxidation potential and thereby lowers
reactivity with singlet oxygen, and as a result, light stability in
a color conversion film that does not use a barrier film is
significantly enhanced. Accordingly, by using the metal complex
described in the present specification as a fluorescent material of
a color conversion film, a color conversion film having excellent
luminance and Color Gamut, and having a simple manufacturing
process and low unit manufacturing costs by not using a barrier
film can be provided.
The compound of Chemical Formula 1 may absorb blue light and
release green light depending on a substituent.
According to one example, the compound of Chemical Formula 1 has a
maximum light emission peak present in 520 nm to 550 nm in a film
state. Such a compound emits green light.
According to one example, the compound of Chemical Formula 1 has a
maximum light emission peak present in 520 nm to 550 nm in a film
state, and a half-width of the light emission peak is 50 nm or
less. Having such a small half-width may further increase Color
Gamut. Herein, the light emission peak of the compound of Chemical
Formula 1 may have a half-width of 5 nm or more.
According to one example, the compound of Chemical Formula 1 has a
maximum light emission peak present in 610 nm to 650 nm in a film
state. Such a compound emits red light.
According to one example, the compound of Chemical Formula 1 has a
maximum light emission peak present in 610 nm to 650 nm in a film
state, and a half-width of the light emission peak is 60 nm or
less. Having such a small half-width may further increase Color
Gamut. Herein, the light emission peak of the compound of Chemical
Formula 1 may have a half-width of 5 nm or more.
According to one example, the compound of Chemical Formula 1 has
quantum efficiency of 0.9 or more.
In the present specification, a "film state" means a state prepared
in a film form instead of a solution state, using the compound of
Chemical Formula 1 alone, or as a mixture with other components
that do not affect half-width and quantum efficiency
measurements.
In the present specification, the half-width means a width of a
light emission peak at half the maximum height in a maximum light
emission peak of light emitting from the compound of Chemical
Formula 1.
In the present specification, the quantum efficiency may be
measured using methods known in the art, and for example, may be
measured using an integrating sphere.
Examples of the substituents of Chemical Formula 1 are described
below, however, the substituents are not limited thereto.
The term "substituted or unsubstituted" in the present
specification means being substituted with one or more substituents
selected from the group consisting of deuterium; a halogen group; a
nitrile group; a nitro group; a carbonyl group; a carboxyl group;
an ester group; an imide group; an amide group; a sulfonate group;
a substituted or unsubstituted alkynyl group; a substituted or
unsubstituted alkyl group; a substituted or unsubstituted
cycloalkyl group; a substituted or unsubstituted alkoxy group; a
substituted or unsubstituted aryloxy group; a substituted or
unsubstituted alkylthioxy group; a substituted or unsubstituted
arylthioxy group; a substituted or unsubstituted alkylsulfoxy
group; a substituted or unsubstituted arylsulfoxy group; a
substituted or unsubstituted alkenyl group; a substituted or
unsubstituted silyl group; a substituted or unsubstituted boron
group; a substituted or unsubstituted arylphosphine group; a
substituted or unsubstituted phosphine oxide group; a substituted
or unsubstituted arylalkyl group; a substituted or unsubstituted
alkylaryl group; a substituted or unsubstituted aryl group; or a
substituted or unsubstituted aromatic or aliphatic heterocyclic
group including one or more of N, O and S atoms, or having no
substituents, or being substituted with a substituent linking two
or more substituents among the substituents illustrated above, or
having no substituents. For example, "a substituent linking two or
more substituents" may include a biphenyl group. In other words, a
biphenyl group may be an aryl group, or interpreted as a
substituent linking two phenyl groups.
The term "substitution" means a hydrogen atom bonding to a carbon
atom of a compound is changed to another substituent, and the
position of substitution is not limited as long as it is a position
at which a hydrogen atom is substituted, that is, a position at
which a substituent may substitute, and when two or more
substituents substitute, the two or more substituents may be the
same as or different from each other.
In the present specification, examples of the halogen group include
fluorine, chlorine, bromine or iodine.
In the present specification, in the carbonyl group, (--C.dbd.O)
may be substituted with a substituted or unsubstituted alkyl group,
a substituted or unsubstituted arylalkyl group, a substituted or
unsubstituted alkylaryl group, or a substituted or unsubstituted
aryl group.
In the present specification, in the ester group, oxygen of the
ester group may be substituted with a substituted or unsubstituted
alkyl group, a substituted or unsubstituted arylalkyl group, a
substituted or unsubstituted alkylaryl group, or a substituted or
unsubstituted aryl group. Specifically, compounds having the
following structural formulae may be included, but the compound is
not limited thereto.
##STR00005##
In the present specification, the number of carbon atoms of the
imide group is not particularly limited, but is preferably 1 to 25.
Specifically, compounds having the following structures may be
included, but the compound is not limited thereto.
##STR00006##
In the present specification, in the amide group, nitrogen of the
amide group may be once or twice substituted with hydrogen, a
substituted or unsubstituted alkyl group, a substituted or
unsubstituted arylalkyl group, a substituted or unsubstituted
alkylaryl group, or a substituted or unsubstituted aryl group.
Specifically, compounds having the following structural formulae
may be included, but the compound is not limited thereto.
##STR00007##
In the present specification, the sulfonate group may be expressed
as --SO.sub.3X, and X may be hydrogen or a group 1 element. For
example, the sulfonate group includes --SO.sub.3Na.
In the present specification, the alkynyl group may be linear or
branched, and although not particularly limited thereto, the number
of carbon atoms is preferably 2 to 50.
In the present specification, the alkyl group may be linear or
branched, and the number of carbon atoms is not particularly
limited, but is preferably 1 to 50. Specific examples thereof
include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl,
isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl,
pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl,
n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl,
3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl,
cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl,
1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl,
2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl,
2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are
not limited thereto.
In the present specification, the cycloalkyl group is not
particularly limited, but preferably has 3 to 60 carbon atoms.
Specific examples thereof include cyclopropyl, cyclobutyl,
cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl,
cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl,
2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl,
4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but
are not limited thereto.
In the present specification, the alkoxy group may be linear,
branched or cyclic. The number of carbon atoms of the alkoxy group
is not particularly limited, but is preferably 1 to 20. Specific
examples thereof may include methoxy, ethoxy, n-propoxy,
isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy,
sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy,
3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy,
n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but are not
limited thereto.
In the present specification, the alkenyl group may be linear or
branched, and although not particularly limited thereto, the number
of carbon atoms is preferably 2 to 40. Specific examples thereof
may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl,
3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl,
1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl,
2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl,
2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, a styrenyl
group and the like, but are not limited thereto.
In the present specification, the aryl group may be a monocyclic
aryl group or a multicyclic aryl group, and includes cases
substituted with an alkyl group having 1 to 25 carbon atoms or an
alkoxy group having 1 to 25 carbon atoms. In addition, the aryl
group in the present specification may mean an aromatic ring.
When the aryl group is a monocyclic aryl group, the number of
carbon atoms is not particularly limited, but is preferably 6 to
25. Specific examples of the monocyclic aryl group may include a
phenyl group, a biphenyl group, a terphenyl group and the like, but
are not limited thereto.
When the aryl group is a multicyclic aryl group, the number of
carbon atoms is not particularly limited, but is preferably 10 to
24. Specific example of the multicyclic aryl group may include a
naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl
group, a perylenyl group, a crycenyl group, a fluorenyl group and
the like, but are not limited thereto.
In the present specification, the fluorenyl group may be
substituted, and adjacent substituents may bond to each other to
form a ring.
When the fluorenyl group is substituted,
##STR00008## and the like may be included. However, the structure
is not limited thereto.
In the present specification, the silyl group may be expressed as
--SiRR'R'', and R, R' and R'' may be each independently hydrogen, a
linear, branched or cyclic alkyl group having 1 to 25 carbon atoms,
or an aryl group having 6 to 25 carbon atoms. Specific examples
thereof include a trimethylsilyl group, a triethylsilyl group, a
t-butyldimethylsilyl group, a vinyldimethylsilyl group, a
propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl
group, a phenylsilyl group and the like, but are not limited
thereto.
In the present specification, the boron group may be expressed as
--BRR', and R and R' may be each independently hydrogen, a linear,
branched or cyclic alkyl group having 1 to 25 carbon atoms, or an
aryl group having 6 to 25 carbon atoms.
In the present specification, examples of the arylphosphine group
include a substituted or unsubstituted monoarylphosphine group, a
substituted or unsubstituted diarylphosphine group, or a
substituted or unsubstituted triarylphosphine group. The aryl group
in the arylphosphine group may be a monocyclic aryl group or a
multicyclic aryl group. The arylphosphine group including two or
more aryl groups may include a monocyclic aryl group, a multicyclic
aryl group, or both a monocyclic aryl group and a multicyclic aryl
group.
In the present specification, the heterocyclic group is a
heterocyclic group including one or more of O, N and S as a
heteroatom, and although not particularly limited thereto, the
number of carbon atoms is preferably 2 to 60. Examples of the
heterocyclic group include a thiophene group, a furan group, a
pyrrole group, an imidazole group, a triazole group, an oxazole
group, an oxadiazole group, a pyridyl group, a bipyridyl group, a
pyrimidyl group, a triazine group, a triazole group, an acridyl
group, a pyridazine group, a pyrazinyl group, a qinolinyl group, a
quinazoline group, a quinoxalinyl group, a phthalazinyl group, a
pyridopyrimidinyl group, a pyridopyrazinyl group, a
pyrazinopyrazinyl group, an isoquinoline group, an indole group, a
carbazole group, a benzoxazole group, a benzimidazole group, a
benzothiazole group, a benzocarbazole group, a benzothiophene
group, a dibenzothiophene group, a benzofuranyl group, a
phenanthroline group, a thiazolyl group, an isoxazolyl group, an
oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a
phenothiazinyl group, a dibenzofuranyl group and the like, but are
not limited thereto.
In the present specification, the aryl group in the arylalkyl
group, the alkylaryl group, the arylalkoxy group, the aryloxy
group, the arylthioxy group, the arylsulfoxy group and the
aralkylamine group is the same as the examples of the aryl group
described above. Specific examples of the aryloxy group include
phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy,
2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy,
4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy,
4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy,
2-anthryloxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy,
9-phenanthryloxy and the like, examples of the arylthioxy group
include a phenylthioxy group, a 2-methylphenylthioxy group, a
4-tert-butylphenylthioxy group and the like, and examples of the
arylsulfoxy group include a benzenesulfoxy group, a
p-toluenesulfoxy group and the like, but the examples are not
limited thereto.
In the present specification, the alkyl group in the arylalkyl
group, the alkylaryl group, the alkylthioxy group and the
alkylsulfoxy group is the same as the examples of the alkyl group
described above. Specific examples of the alkylthioxy group include
a methylthioxy group, an ethylthioxy group, a tert-butylthioxy
group, a hexylthioxy group, an octylthioxy group and the like, and
examples of the alkylsulfoxy group include a methylsulfoxy group,
an ethylsulfoxy group, a propylsulfoxy group, a butylsulfoxy group
and the like, but the examples are not limited thereto.
In the present specification, the alkoxy group in the arylalkoxy
group is the same as the examples of the alkoxy group described
above.
According to one embodiment of the present application, R.sub.1 to
R.sub.4 of Chemical Formula 1 are the same as or different from
each other, and each independently hydrogen, deuterium, a
substituted or unsubstituted alkyl group, a substituted or
unsubstituted alkylaryl group, a substituted or unsubstituted
arylalkyl group, a substituted or unsubstituted aryl group, or one
of the following structural formulae.
##STR00009##
Definitions of R.sub.8 to R.sub.13 are the same as those described
above.
According to one embodiment of the present application, R.sub.1 to
R.sub.4 of Chemical Formula 1 are the same as or different from
each other, and each independently hydrogen, deuterium, a
substituted or unsubstituted alkyl group, a substituted or
unsubstituted alkylaryl group, a substituted or unsubstituted
arylalkyl group, or a substituted or unsubstituted aryl group.
According to one embodiment of the present application, R.sub.1 to
R.sub.4 of Chemical Formula 1 are the same as or different from
each other, and each independently hydrogen, deuterium, an alkyl
group unsubstituted or substituted with a halogen group, an
alkylaryl group, an arylalkyl group, or an aryl group.
According to one embodiment of the present application, R.sub.1 to
R.sub.4 of Chemical Formula 1 are the same as or different from
each other, and each independently an alkyl group unsubstituted or
substituted with fluorine, an alkylaryl group, an arylalkyl group,
or an aryl group.
According to one embodiment of the present application, R.sub.1 to
R.sub.4 of Chemical Formula 1 are the same as or different from
each other, and each independently a methyl group unsubsituted or
substituted with fluorine; a t-butyl group; a phenyl group
unsubstituted or substituted with a group selected from the group
consisting of a methyl group, a t-butyl group and a methoxy group;
a biphenyl group unsubstituted or substituted with a t-butyl
group.
According to one embodiment of the present application, at least
one of R.sub.1 to R.sub.4 of Chemical Formula 1 is one of the
following structural formulae.
##STR00010##
Definitions of R.sub.8 to R.sub.13 are the same as those described
above.
According to one embodiment of the present application, R.sub.1 and
R.sub.2 are the same, and R.sub.3 and R.sub.4 are the same in
Chemical Formula 1.
According to one embodiment of the present application, R.sub.1 and
R.sub.2 are the same, R.sub.3 and R.sub.4 are the same, and R.sub.1
and R.sub.4 are different in Chemical Formula 1.
According to one embodiment of the present application, R.sub.1 and
R.sub.4 are the same, and R.sub.2 and R.sub.3 are the same in
Chemical Formula 1.
According to one embodiment of the present application, R.sub.1 and
R.sub.4 are the same, R.sub.2 and R.sub.3 are the same, and R.sub.1
and R.sub.2 are different in Chemical Formula 1.
According to one embodiment of the present application, R.sub.1 to
R.sub.4 of Chemical Formula 1 are the same.
According to one embodiment of the present application, R.sub.5 of
Chemical Formula 1 is hydrogen, deuterium, or one of the following
structural formulae.
##STR00011##
Definitions of R.sub.8 to R.sub.13 are the same as those described
above.
According to one embodiment of the present application, R.sub.6 of
Chemical Formula 1 is hydrogen; a substituted or unsubstituted
alkyl group; a substituted or unsubstituted cycloalkyl group; a
substituted or unsubstituted alkoxy group; a substituted or
unsubstituted aryl group; a substituted or unsubstituted alkylaryl
group; or a substituted or unsubstituted aromatic or aliphatic
heterocyclic group.
According to one embodiment of the present application, R.sub.6 of
Chemical Formula 1 is hydrogen; a nitrile group; an alkyl group
unsubstituted or substituted with a halogen group or an aryl group;
a cycloalkyl group; an alkoxy group; an aryl group unsubstituted or
substituted with a group selected from the group consisting of a
halogen group, a nitrile group, an ester group, an alkynyl group,
an alkyl group, an alkoxy group, an aryloxy group and an aryl
group, or substituted with a group bonding two or more selected
from the group described above; or an aromatic or aliphatic
heterocyclic group unsubstituted or substituted with a group
selected from the group consisting of a halogen group, a nitrile
group, an ester group, an alkynyl group, an alkyl group, an alkoxy
group, an aryloxy group and an aryl group, or substituted with a
group bonding two or more selected from the group described
above.
According to one embodiment of the present application, R.sub.6 of
Chemical Formula 1 is hydrogen; a nitrile group; a methyl group
substituted with a halogen group or an aryl group; a propyl group
substituted with a halogen group; a cyclohexyl group; a propoxy
group; a phenyl group unsubstituted or substituted with a group
selected from the group consisting of a halogen group, a nitrile
group, an ester group, an alkynyl group, an alkyl group, an alkoxy
group, an aryloxy group and an aryl group, or substituted with a
group bonding two or more selected from the group described above;
a biphenyl group unsubstituted or substituted with a group
consisting of a halogen group, a nitrile group, an ester group, an
alkynyl group, an alkyl group, an alkoxy group, an aryloxy group
and an aryl group, or substituted with a group bonding two or more
selected from the group described above; a terphenyl group
unsubstituted or substituted with a group consisting of a halogen
group, a nitrile group, an ester group, an alkynyl group, an alkyl
group, an alkoxy group, an aryloxy group and an aryl group, or
substituted with a group bonding two or more selected from the
group described above; or a dibenzofuran group unsubstituted or
substituted with a group consisting of a halogen group, a nitrile
group, an ester group, an alkynyl group, an alkyl group, an alkoxy
group and an aryl group, or substituted with a group bonding two or
more selected from the group described above.
According to one embodiment of the present application, R.sub.6 of
Chemical Formula 1 is hydrogen; a nitrile group; a methyl group
substituted with fluorine or a phenyl group; a propyl group
substituted with fluorine; a cyclohexyl group; a propoxy group; a
phenyl group unsubstituted or substituted with a group selected
from the group consisting of a methyl group, a pentyloxy group
substituted with a carboxyl group, an ethoxy group substituted with
an ethoxy group substituted with a methoxy group, a methoxy group,
a dibenzofuran group, a terphenyl group substituted with a t-butyl
group, a terphenyl group substituted with a carboxyl group, and a
propylester group; a biphenyl group unsubstituted or substituted
with a group selected from the group consisting of a nitrile group,
a methyl group, a phenyl group substituted with a t-butyl group,
and a phenyl group substituted with a carboxyl group; or a
terphenyl group unsubstituted or substituted with a group selected
from the group consisting of a methyl group, a t-butyl group, a
phenyl group substituted with a t-butyl group, a carboxyl group,
and a phenyl group substituted with a carboxyl group.
According to one embodiment of the present application, R.sub.8 and
R.sub.11 are the same as or different from each other, and each
independently hydrogen; deuterium; a substituted or unsubstituted
alkyl group; a substituted or unsubstituted cycloalkyl group; a
substituted or unsubstituted arylalkyl group; a substituted or
unsubstituted alkylaryl group; a substituted or unsubstituted aryl
group; or a substituted or unsubstituted aromatic or aliphatic
heterocyclic group.
According to one embodiment of the present application, R.sub.8 and
R.sub.11 are the same as or different from each other, and each
independently a substituted or unsubstituted alkyl group; a
substituted or unsubstituted cycloalkyl group; a substituted or
unsubstituted arylalkyl group; a substituted or unsubstituted
alkylaryl group; a substituted or unsubstituted aryl group; or a
substituted or unsubstituted aromatic or aliphatic heterocyclic
group.
According to one embodiment of the present application, R.sub.8 and
R.sub.11 are the same as or different from each other, and each
independently a substituted or unsubstituted alkyl group; a
substituted or unsubstituted cycloalkyl group; a substituted or
unsubstituted arylalkyl group; a substituted or unsubstituted
alkylaryl group; a substituted or unsubstituted aryl group; or a
substituted or unsubstituted aromatic or aliphatic heterocyclic
group, and when these are substituted, the substituent is a group
selected from the group consisting of a halogen group; a nitrile
group; a carboxyl group; an ester group; an alkyl group; a
cycloalkyl group; an alkoxy group; an aryloxy group; an arylalkyl
group; an alkylaryl group; an aryl group; or an aromatic and
aliphatic heterocyclic group, or a group bonding two or more of the
groups selected from the group described above.
According to one embodiment of the present application, R.sub.8 and
R.sub.11 are the same as or different from each other, and each
independently an alkyl group unsubstituted or substituted with a
group selected from the group consisting of a halogen group, a
nitrile group, a carboxyl group, an aryl group and a heterocyclic
group; an alkylaryl group; a heterocyclic group substituted with an
aryl group.
According to one embodiment of the present application, R.sub.8 and
R.sub.11 are the same as or different from each other, and each
independently a methyl group unsubstituted or substituted with a
group selected from the group consisting of a phenyl group, a
biphenyl group, a phenyl group substituted with a naphthyl group, a
phenyl group substituted with a dibenzofuran group, a phenyl group
substituted with fluorine, a phenyl group substituted with a
trifluoromethyl group, a phenyl group substituted with an
anthracene group substituted with a phenyl group, a phenyl group
substituted with a nitrile group, and a phenyl group substituted
with a carboxyl group; an ethyl group unsubstituted or substituted
with a group selected from the group consisting of a phenoxy group
substituted with an anthracene group substituted with a phenyl
group, a carboxyl group, a phenothiazine group, a naphthyloxy
group, a triazineoxy group substituted with a phenyl group, and a
pyrimidineoxy group substituted with a phenyl group; an n-propyl
group; an n-butyl group unsubstituted or substituted with fluorine;
a pentyl group unsubstituted or substituted with fluorine; a phenyl
group unsubstituted or substituted with a group selected from the
group consisting of a t-butyl group and a methyl group; a naphthyl
group; or a carbazolyl group unsubstituted or substituted with a
phenyl group.
According to one embodiment of the present application, R.sub.9 and
R.sub.10 are the same as or different from each other, and each
independently hydrogen; deuterium; a substituted or unsubstituted
alkyl group; a substituted or unsubstituted cycloalkyl group; a
substituted or unsubstituted arylalkyl group; a substituted or
unsubstituted alkylaryl group; a substituted or unsubstituted aryl
group; or a substituted or unsubstituted aromatic or aliphatic
heterocyclic group, or bond to each other to form an aliphatic or
aromatic ring.
According to one embodiment of the present application, R.sub.9 and
R.sub.10 are the same as or different from each other, and each
independently hydrogen; deuterium; an alkyl group; a cycloalkyl
group; an arylalkyl group unsubstituted or substituted with halogen
or a haloalkyl group; an alkylaryl group; an aryl group
unsubstituted or substituted with halogen or a haloalkyl group; or
an aromatic and aliphatic heterocyclic group, or bond to each other
to form an aliphatic ring.
According to one embodiment of the present application, R.sub.9 and
R.sub.10 are the same as or different from each other, and each
independently hydrogen; or a methyl group substituted with a phenyl
group substituted with a trifluoromethyl group, or may bond to each
other to form a phenothiazine ring.
According to one embodiment of the present application, R.sub.12
and R.sub.13 are the same as or different from each other, and each
independently hydrogen; deuterium; a substituted or unsubstituted
alkyl group; a substituted or unsubstituted cycloalkyl group; a
substituted or unsubstituted arylalkyl group; a substituted or
unsubstituted alkylaryl group; a substituted or unsubstituted aryl
group; or a substituted or unsubstituted aromatic or aliphatic
heterocyclic group, or bond to each other to form an aliphatic or
aromatic ring.
According to one embodiment of the present application, R.sub.12
and R.sub.13 are the same as or different from each other, and each
independently hydrogen; deuterium; an alkyl group; a cycloalkyl
group; an arylalkyl group unsubstituted or substituted with halogen
or a haloalkyl group; an alkylaryl group; an aryl group
unsubstituted or substituted with halogen or a haloalkyl group; or
an aromatic and aliphatic heterocyclic group, or bond to each other
to form an aliphatic ring.
According to one embodiment of the present application, X.sub.1 and
X.sub.2 are the same as or different from each other, and each
independently F; a nitrile group; a substituted or unsubstituted
alkynyl group; a substituted or unsubstituted alkyl group; a
substituted or unsubstituted alkoxy group; a substituted or
unsubstituted aryloxy group; a substituted or unsubstituted aryl
group; or a substituted or unsubstituted aromatic or aliphatic
heterocyclic group, or bond to each other to form an aromatic or
aliphatic ring.
According to one embodiment of the present application, X.sub.1 and
X.sub.2 are the same as or different from each other, and each
independently F; a nitrile group; an alkynyl group unsubstituted or
substituted with an aryl group or an alkylaryl group; an alkoxy
group unsubstituted or substituted with a halogen group; an aryl
group unsubstituted or substituted with a halogen group or a
heterocyclic group; or an aromatic or aliphatic heterocyclic group
unsubstituted or substituted with an aryl group, or bond to each
other to form a monocyclic or multicyclic aromatic or aliphatic
ring.
According to one embodiment of the present application, X.sub.1 and
X.sub.2 are the same as or different from each other, and each
independently F; a nitrile group; an ethynyl group substituted with
a triiso-propylsilyl group; or an ethynyl group substituted with a
phenyl group substituted with a t-butyl group.
According to one embodiment of the present application, X.sub.3 is
a halogen group; a nitrile group; an ester group; an alkyl group;
an alkoxy group substituted with a fluoro group; or a fluoroalkyl
group.
According to one embodiment of the present application, X.sub.3 is
F; a nitrile group; a methoxy group; a trifluoromethyl group; a
methylester group; or an n-butoxy group substituted with a fluoro
group.
According to one embodiment of the present application, Y.sub.1 to
Y.sub.4 are the same as or different from each other, and each
independently CH, CF or N.
According to one embodiment of the present application, R.sub.101
to R.sub.104 are the same as or different from each other, and each
independently hydrogen; deuterium; a halogen group; a nitrile
group; an ester group; a substituted or unsubstituted alkyl group;
a substituted or unsubstituted alkylaryl group; a substituted or
unsubstituted arylalkyl group; or a substituted or unsubstituted
aryl group.
According to one embodiment of the present application, R.sub.101
to R.sub.104 are the same as or different from each other, and each
independently hydrogen; deuterium; a halogen group; a nitrile
group; an ester group; an alkyl group unsubstituted or substituted
with halogen; an alkylaryl group; an arylalkyl group; or an aryl
group.
According to one embodiment of the present application, R.sub.101
to R.sub.104 are the same as or different from each other, and each
independently hydrogen; or F.
According to one embodiment of the present application, Chemical
Formula 1 may be represented by one of the following structural
formulae.
##STR00012## ##STR00013## ##STR00014## ##STR00015## ##STR00016##
##STR00017## ##STR00018## ##STR00019## ##STR00020## ##STR00021##
##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026##
##STR00027## ##STR00028## ##STR00029## ##STR00030##
##STR00031##
Another embodiment of the present application provides a color
conversion film including a resin matrix; and the compound of
Chemical Formula 1 dispersed into the resin matrix.
Content of the compound of Chemical Formula 1 in the color
conversion film may be in a range of 0.001 wt % to 10 wt %.
The color conversion film may include one type of the compound of
Chemical Formula 1, or two or more types thereof. For example, the
color conversion film may include one type of the compound emitting
green color among the compounds of Chemical Formula 1. As another
example, the color conversion film may include one type of the
compound emitting red color among the compounds of Chemical Formula
1. As still another example, the color conversion film may include
one type of the compound emitting green color and one type of the
compound emitting red color among the compounds of Chemical Formula
1.
The color conversion film may further include additional
fluorescent materials in addition to the compound of Chemical
Formula 1. When using a light source emitting blue light, the color
conversion film preferably includes both a green light emitting
fluorescent material and a red light emitting fluorescent material.
In addition, when using a light source emitting blue light and
green light, the color conversion film may include only a red light
emitting fluorescent material. However, the case is not limited
thereto, and even when using a light source emitting blue light,
the color conversion film may include only a red light emitting
compound when laminating a separate film including a green light
emitting fluorescent material. On the other hand, even when using a
light source emitting blue light, the color conversion film may
include only a green light emitting compound when laminating a
separate film including a red light emitting fluorescent
material.
The color conversion film may further include an additional layer
including a resin matrix; and a compound dispersed into the resin
matrix and emitting light having a wavelength different from the
compound of Chemical Formula 1. The compound emitting light having
a wavelength different from the compound of Chemical Formula 1 may
also be a compound represented by Chemical Formula 1, or may be a
different known fluorescent material.
Materials of the resin matrix are preferably a thermoplastic
polymer or a thermocuring polymer. Specifically, poly(meth)acryl
series such as polymethyl methacrylate (PMMA), polycarbonate series
(PC), polystyrene series (PS), polyarylene series (PAR),
polyurethane series (TPU), styrene-acrylonitrile series (SAN),
polyvinylidene fluoride series (PVDF), modified polyvinylidene
fluoride series (modified-PVDF) and the like may be used as
materials of the resin matrix.
According to another embodiment of the present application, the
color conversion film according to the embodiments described above
further includes light diffusion particles. By dispersing light
diffusion particles into the color conversion film to enhance
luminance instead of a light diffusion film used in the art, an
attaching process may not be included and higher luminance may be
obtained as well compared to cases using a separate light diffusion
film.
As the light diffusion particles, particles having a high
refractive index with the resin matrix may be used, and examples
thereof include TiO.sub.2, silica, borosilicate, alumina, sapphire,
air or other gases, air- or gas-filled porous beads or particles
(for example, air/gas-filled glass or polymer); polystyrene,
polycarbonate, polymethyl methacrylate, acryl, methyl methacrylate,
styrene, a melamine resin, a formaldehyde resin, or polymer
particles including melamine and formaldehyde resins, or any
suitable combination thereof.
Particle diameters of the light diffusion particles are in a range
of 0.1 micrometers to 5 micrometers, for example, in a range of 0.3
micrometers to 1 micrometer. Content of the light diffusion
particles may be determined as necessary, and for example, may be
in a range of approximately 1 to 30 parts by weight based on 100
parts by weight of the resin matrix.
The color conversion film according to the embodiments described
above may have a thickness of 2 micrometers to 200 micrometers.
Particularly, the color conversion film is capable of exhibiting
high luminance even with a small thickness of 2 micrometers to 20
micrometers. This is due to the fact that the content of the
fluorescent material molecules included in the unit volume is
higher than the content of quantum dots.
The color conversion film according to the embodiments described
above may be provided with a substrate on one surface. This
substrate may function as a support when preparing the color
conversion film. The type of the substrate is not particularly
limited, and materials and thicknesses thereof are not limited as
long as the substrate is transparent and capable of functioning as
a support. Herein, being transparent means visible ray
transmissivity of 70% or more. For example, a PET film may be used
as the substrate.
The color conversion film described above may be prepared by
coating a resin solution dissolving the compound of Chemical
Formula 1 described above on a substrate and drying the result, or
extruding the compound of Chemical Formula 1 described above with a
resin, and filming the result.
The compound of Chemical Formula 1 described above is dissolved in
the resin solution, and therefore, the compound of Chemical Formula
1 is uniformly distributed in the solution. This is different from
a quantum dot film preparation process requiring a separate
dispersion process.
The resin solution dissolving the compound of Chemical Formula 1 is
not particularly limited in the preparation method as long as the
compound of Chemical Formula 1 described above is dissolved in the
resin solution.
According to one example, the resin solution dissolving the
compound of Chemical Formula 1 may be prepared using a method of
preparing a first solution by dissolving the compound of Chemical
Formula 1 in a solvent, preparing a second solution by dissolving a
resin in a solvent, and mixing the first solution and the second
solution. When the first solution and the second solution are
mixed, these preferably are homogeneously mixed. However, the
method is not limited thereto, and a method of adding and
dissolving the compound of Chemical Formula 1 and a resin in a
solvent at the same time, a method of dissolving the compound of
Chemical Formula 1 in a solvent and then adding and dissolving a
resin thereto, a method of dissolving a resin in a solvent and then
adding and dissolving the compound of Chemical Formula 1 thereto,
and the like, may be used.
As the resin included in the solution, the resin matrix material
described above, a monomer capable of being cured using this resin
matrix, or a mixture thereof, may be used. For example, the monomer
capable of being cured using this resin matrix includes a
(meth)acryl-based monomer, and this may be formed to a resin matrix
material through UV curing. When using such a curable monomer, an
initiator required for the curing may be further added as
necessary.
The solvent is not particularly limited as long as the solvent is
capable of being removed by drying afterwords without exercising a
bad influence on the coating process. Nonlimiting examples of the
solvent include toluene, xylene, acetone, chloroform, various
alcohol-based solvents, methylethyl ketone (MEK), methylisobutyl
ketone (MIBK), ethyl acetate (EA), butyl acetate, dimethylformamide
(DMF), dimethylacetamide (DMAc), dimethyl sulfoxide (DMSO),
N-methyl-pyrrolidone (NMP) and the like, and one type, or a mixture
of two or more types may be used. When the first solution and the
second solution are used, solvents included in each of the
solutions may be the same as or different from each other. Even
when different types of solvents are used in the first solution and
the second solution, these solvents preferably have compatibility
so as to be mixed to each other.
The process of coating the resin solution dissolving the compound
of Chemical Formula 1 on a substrate may use a roll-to-roll
process. For example, a process of unwinding a substrate from a
substrate-wound roll, coating the resin solution dissolving the
compound of Chemical Formula 1 on one surface of the substrate,
drying the result, and then winding the result again on a roll may
be used. When using a roll-to-roll process, viscosity of the resin
solution is preferably determined within a range capable of
carrying out the above-mentioned process, and for example, the
viscosity may be determined within a range of 200 cps to 2,000
cps.
As the coating method, various known methods may be used, and for
example, a die coater may be used, or various bar coating methods
such as a comma coater and a reverse comma coater may be used.
After the coating, a drying process is carried out. The drying
process may be carried out under a condition required for removing
the solvent. For example, a color conversion film including a
fluorescent material including the compound of Chemical Formula 1
having a target thickness and concentration may be obtained on a
substrate by carrying out drying under a condition sufficiently
removing a solvent in an oven placed adjacent to a coater in a
direction of a substrate progressing during a coating process.
When a monomer that is capable of being cured with the resin matrix
resin is used as a resin included in the solution, curing, for
example, UV curing, may be carried out prior to or at the same time
with the drying.
When filming the compound of Chemical Formula 1 with a resin
through extrusion, extrusion methods known in the art may be used,
and for example, a color conversion film may be prepared by
extruding the compound of Chemical Formula 1 with a resin such as
polycarbonate series (PC), poly(meth)acryl series and
styrene-acrylonitrile series (SAN).
According to another embodiment of the present application, the
color conversion film may be provided with a protective film or a
barrier film on at least one surface. As the protective film and
the barrier film, those known in the art may be used.
Another embodiment of the present application provides a backlight
unit including the color conversion film described above. The
backlight unit may have a backlight unit constitution known in the
art except that it includes the color conversion film described
above. FIG. 1 shows a mimetic view of a backlight unit structure
according to one example. The backlight unit according to FIG. 1
includes a side chain-type light source (blue color), a reflective
plate surrounding the light source (green color), a light guide
plate (apricot color) directly emitting light from the light
source, or inducing light reflected from the reflective plate, a
reflective layer (sky blue color) provided on one surface of the
light guide plate, and a color conversion film (white color)
provided on the opposite surface of a surface facing the reflective
layer of the light guide plate. However, the scope of the present
invention is not limited to FIG. 1, and the light source may use a
direct type as well as a side chain type, and the reflective plate
or the reflective layer may not be included or may be replaced with
other constitutions, and as necessary, additional films such as a
light diffusion film, a light collecting film, a luminance
enhancing film and the like may be further provided.
Another embodiment of the present application provides a display
device including the backlight unit. The display device is not
particularly limited as long as it includes the backlight unit, and
may be included in TVs, computer monitors, laptops, mobile phones
and the like.
Hereinafter, the present invention will be described with reference
to examples. However, the examples below are for illustrative
purposes only, and the scope of the present invention is not
limited thereto.
REFERENCE EXAMPLES 1 TO 3
In order to examine spectroscopic properties and light stability of
the following Compounds 1 to 3 and 1-40, light emission spectra in
a solution state (toluene 1.times.10.sup.-5 M) were measured, and
stability of the molecules themselves for light was evaluated
through absorbance differences by time by measuring UV-vis spectra
under a blue backlight.
##STR00032##
FIG. 2 shows light emission spectra (toluene 1.times.10.sup.-5 M)
of Compound 1 (dotted line) and Compound 2 (straight line). As
shown in FIG. 2, it was identified that, when ortho-fluorophenyl
substitutes, the light emission wavelength was suitable for green
compared to Compound 2, and the half-width significantly
decreased.
FIG. 3 and FIG. 4 each show changes in the UV-vis spectra of
Compound 1 and Compound 3 by time under blue light. FIG. 5 shows
absorbance variation in the maximum absorption wavelengths of
Compound 1 (.box-solid.) and Compound 3 (.diamond-solid.) by time
(toluene 1.times.10.sup.-5 M). It was seen that Compound 1
substituted with ortho-fluorophenyl had smaller changes in the
absorbance by time compared to Compound 3 that was not substituted.
This supports the fact that light stability is significantly
enhanced when introducing an ortho-fluorophenyl group.
FIG. 6 shows changes in the UV-vis spectra of Compound 1-40 by time
under blue light. FIG. 7 shows absorbance variation in the maximum
absorption wavelengths of Compound 1 (.box-solid.) and Compound
1-40 (.circle-solid.) (toluene 1.times.10.sup.-5 M). Compound 1-40
additionally introducing an ester group to
ortho-fluorophenyl-substituted Compound 1 had almost no changes in
the absorbance by time under a blue light source. Accordingly, the
structure of Chemical Formula 1 introducing an ortho-fluorophenyl
group and an electron withdrawing group at the same time may play a
role of a green fluorescent substance with significantly enhanced
light stability. When a color conversion film using such compounds
is used for display materials, Color Gamut and efficiency may
increase, and durability may be significantly enhanced.
SYNTHESIS EXAMPLE 1
Preparation of Compound 1-9
##STR00033## ##STR00034##
Preparation of Compound P1: After mixing 2,4-dimethylpyrrole (10 g,
0.10 mol), mesityl aldehyde (7.8 g, 0.052 mol), trifluoroacetic
acid (2 drops), and dry dichloromethane (500 mL) in a flask, the
result was stirred for 5 hours at room temperature under nitrogen.
After checking the disappearance of the starting materials using
TLC, DDQ (12 g, 0.052 mol) was added thereto at 0.degree. C. The
result was stirred for 1 hour at room temperature, and then
triethylamine (26 g, 0.25 mol) was slowly added dropwise thereto.
After the result was stirred for 30 minutes at room temperature, a
boron trifluoride ethyl ether complex (65 g, 0.46 mol) was slowly
added dropwise thereto. The reactants were stirred for 5 hours at
room temperature, water was added thereto, and the result was
extracted using dichloromethane. The result was dried with
anhydrous magnesium sulfate and filtered, and then vacuum distilled
to remove the solvent. A red compound P1 (7.8 g, 40%) was obtained
through a silica-gel column (hexane/ethyl acetate).
[M-F].sup.+=347
Preparation of Compound P2: After mixing dimethylformamide (4 mL)
and dichloroethane (50 mL) in a flask, the temperature was lowered
to 0.degree. C. Under nitrogen atmosphere, POCl.sub.3 (4 mL) was
slowly added dropwise thereto, and the result was stirred for 30
minutes at room temperature. After adding Compound P1 (3 g, 8.2
mmol) to the reaction solution, the result was warmed to 60.degree.
C. and then stirred for 1 hour. The result was cooled to room
temperature and added to a mixed solution of ice and a saturated
aqueous sodium hydroxide solution. The result was stirred for 2
hours at room temperature, and extracted with chloroform. The
result was dried with anhydrous magnesium sulfate and filtered, and
then vacuum distilled to remove the solvent. Red solid Compound P2
(2.9 g, 89%) was obtained through a silica-gel column (hexane/ethyl
acetate). [M-F].sup.+=375
Preparation of Compound P3: After dissolving Compound P2 (2.1 g,
5.3 mmol) and N-iodosuccinimide (3.6 g, 16 mmol) in DMF in a flask,
the result was stirred for 5 hours at 60.degree. C. After the
result was cooled to room temperature, water was added thereto to
filter solid. The solid was dissolved in CHCl.sub.3, and washed
with a saturated Na.sub.2S.sub.2O.sub.3 solution. The result was
dried with anhydrous magnesium sulfate and then silica filtered.
The result was vacuum distilled to remove the solvent, and dark red
Compound P3 (2.3 g, 83%) was obtained through a silica column
(hexane/ethyl acetate). [M-F].sup.+=501
Preparation of Compound P4: After dissolving Compound P3 (2.0 g,
3.8 mmol) and 1-fluorophenylboronic acid (0.61 g, 4.3 mmol) in
toluene and ethanol, potassium carbonate (K.sub.2CO.sub.3, 1.6 g,
11.5 mmol) and water were added to the reaction solution, and then
tetrakis(triphenylphosphine)palladium (0.2 g, 0.16 mmol) was added
thereto. The result was stirred under reflux for 5 hours and cooled
to room temperature, and then extracted with chloroform. The result
was dried with anhydrous magnesium sulfate and filtered, and then
vacuum distilled to remove the solvent. Dark red solid P4 (1.8 g,
94%) was obtained through a silica-gel column. [M-F].sup.+=469
Preparation of Compound P5: After dissolving Compound P4 (0.60 g,
1.2 mmol) and NH.sub.2SO.sub.3H (0.12 g, 1.2 mol) in
tetrahydrofuran, NaCl.sub.2 (0.11 g, 1.2 mmol) dissolved in water
was slowly added dropwise thereto at 0.degree. C. The result was
stirred for 1 hour at room temperature, a saturated
Na.sub.2S.sub.2O.sub.3 solution was added thereto, and the result
was extracted with chloroform. The result was dried with anhydrous
magnesium sulfate and filtered, and then vacuum distilled to remove
the solvent, and red Compound P5 (0.59 g, 91%) was obtained.
[M-F].sup.+=485
Preparation of Compound 1-9: After dissolving Compound P5 (0.50 g,
0.99 mmol), n-butanol (0.1 g, 1.3 mmol) and DMAP (10 mg, 0.08 mmol)
in dichloromethane, DCC (0.22 g, 1.0 mmol) dissolved in
dichloromethane was slowly added dropwise thereto at 0.degree. C.
The result was stirred for 12 hours at room temperature, a
saturated sodium hydroxide solution was added thereto, and the
result was extracted with chloroform. The result was dried with
anhydrous magnesium sulfate and filtered, and then vacuum distilled
to remove the solvent. Orange solid Compound 1-9 (0.43 g, 76%) was
obtained through a silica-gel column. [M-F].sup.+=541
SYNTHESIS EXAMPLE 2
Preparation of Compound 1-40
##STR00035##
Orange Compound 1-40 (0.43 g, 52%) was obtained in the same manner
as in Synthesis Example 1 except that
2,2,3,3,4,4-heptafluorobutanol (0.31 g, 1.5 mmol) was used instead
of n-butanol. [M-F].sup.+=667
SYNTHESIS EXAMPLE 3
Preparation of Compound 1-41
##STR00036##
After dissolving Compound 1-40 (0.50 g, 0.72 mmol) in
dichloromethane, a boron trifluoride ethyl ether complex (0.31 g,
2.18 mmol) was slowly added dropwise thereto at 0.degree. C. The
result was stirred for 3 hours at room temperature, and then TMSCN
(0.43 g, 4.3 mmol) was added dropwise thereto. The result was
stirred for 5 hours at room temperature, a saturated NaHCO.sub.3
solution was added thereto, and the result was extracted with
chloroform. The result was dried with anhydrous magnesium sulfate
and filtered, and then vacuum distilled to remove the solvent.
Orange solid Compound 1-41 (0.46 g, 90%) was obtained through a
silica-gel column. [M+H].sup.+=701
SYNTHESIS EXAMPLE 4
Preparation of Compound 1-43
##STR00037##
Preparation of Compound P6: Orange Compound P6 (0.51 g, 65%) was
obtained in the same manner as in the preparation of Compound P4 of
Synthesis Example 1, except that 2-trifluoromethyl-phenylboronic
acid (0.31 g, 1.63 mmol) was used instead of fluorophenylboronic
acid. [M-F].sup.+=519
Preparation of Compound P7: Red Compound P7 (0.41 g, 77%) was
obtained in the same manner as in the preparation of Compound P5 of
Synthesis Example 1, except that Compound P6 (0.51 g, 0.94 mmol)
was used instead of Compound P4. [M-F].sup.+=535
Preparation of Compound P8: Orange Compound P8 (0.35 g, 71%) was
obtained in the same manner as in the preparation of Compound 1-9
of Synthesis Example 1, except that 2,2,3,3,4,4-heptafluorobutanol
(0.22 g, 1.09 mmol) was used instead of n-butanol.
[M-F].sup.+=717
Preparation of Compound 1-43: Under nitrogen atmosphere, Compound
P8 (0.31 g, 0.42 mmol) was dissolved in dichloromethane, and then
AlCl.sub.3 (0.10 g, 0.75 mmol) was added thereto at 0.degree. C.
The result was stirred under reflux for 2 hours, and
2,2,3,3,4,4-heptafluorobutanol (1.01 g, 5.04 mmol) was added
dropwise thereto. The result was stirred under reflux for 5 hours,
cooled to room temperature, and the reaction solution was added to
water. The result was extracted with dichloromethane, dried with
anhydrous magnesium sulfate and filtered, and then vacuum distilled
to remove the solvent. Orange solid Compound 1-43 (0.41 g, 88%) was
obtained through a silica-gel column. [M+H].sup.+=1097
EXAMPLE 1
A first solution was prepared by dissolving Compound 1-9 in DMF. A
second solution was prepared by dissolving a thermoplastic resin
SAN in a DMF solvent. The first solution and the second solution
were mixed so that the amount of the organic fluorescent substance
became 0.5 parts by weight based on 100 parts by weight of the SAN,
and then uniformly mixed. Solid content of the mixed solution was
20% by weight, and the viscosity was 200 cps. A color conversion
film was prepared by coating this solution on a PET substrate and
drying the result. The luminance spectrum of the prepared color
conversion film was measured using a spectroradiometer (SR series
manufactured by TOPCON). Specifically, the prepared color
conversion film was laminated on one surface of a light guide plate
of a backlight unit including an LED blue backlight (maximum light
emission wavelength 450 nm) and a light guide plate, then a prism
sheet and a DBEF film were laminated on the color conversion film,
and a luminance spectrum of the film was measured. When measuring
the luminance spectrum, the initial value was set so that
brightness of blue LED light became 600 nit without the color
conversion film.
The color conversion film of Compound 1- 9 emitted light at 547 nm
under blue LED light, and a half-width was 36 nm. A ratio of the
decrease in blue fluorescence to the increase in green fluorescence
after laminating the color conversion film on the blue backlight
was 0.97. Under the driving of the blue backlight, intensity of
green fluorescence decreased by 48% after 400 hours under the
condition of a temperature of 60.degree. C. and 90% RH (FIG.
8).
EXAMPLE 2
A color conversion film was prepared using Compound 1- 40 according
to the method of Example 1. The color conversion film of the
compound emitted light at 546 nm under blue LED light, and a
half-width was 36 nm. A ratio of the decrease in blue fluorescence
to the increase in green fluorescence after laminating the color
conversion film on the blue backlight was 0.99. Under the driving
of the blue backlight, intensity of green fluorescence decreased by
22% after 400 hours under the condition of a temperature of
60.degree. C. and 90% RH (FIG. 8).
EXAMPLE 3
A color conversion film was prepared using Compound 1- 41 according
to the method of Example 1. The color conversion film of the
compound emitted light at 545 nm under blue LED light, and a
half-width was 36 nm. A ratio of the decrease in blue fluorescence
to the increase in green fluorescence after laminating the color
conversion film on the blue backlight was 0.98. Under the driving
of the blue backlight, intensity of green fluorescence decreased by
23% after 400 hours under the condition of a temperature of
60.degree. C. and 90% RH (FIG. 8).
EXAMPLE 4
A color conversion film was prepared using Compound 1- 43 according
to the method of Example 1. The color conversion film of the
compound emitted light at 539 nm under blue LED light, and a
half-width was 35 nm. A ratio of the decrease in blue fluorescence
to the increase in green fluorescence after laminating the color
conversion film on the blue backlight was 0.97. Under the driving
of the blue backlight, intensity of green fluorescence decreased by
32% after 400 hours under the condition of a temperature of
60.degree. C. and 90% RH (FIG. 8).
COMPARATIVE EXAMPLE 1
A color conversion film was prepared using Compound 1 according to
the method of Example 1. The color conversion film of the compound
emitted light at 540 nm under blue LED light, and a half-width was
40 nm. A ratio of the decrease in blue fluorescence to the increase
in green fluorescence after laminating the color conversion film on
the blue backlight was 0.96. Under the driving of the blue
backlight, intensity of green fluorescence decreased to 50% or less
after 70 hours under the condition of a temperature of 60.degree.
C. and 90% RH (FIG. 8).
COMPARATIVE EXAMPLE 2
A color conversion film was prepared using Compound 3 according to
the method of Example 1. The color conversion film of the compound
emitted light at 535 nm under blue LED light, and a half-width was
41 nm. A ratio of the decrease in blue fluorescence to the increase
in green fluorescence after laminating the color conversion film on
the blue backlight was 0.95. Under the driving of the blue
backlight, intensity of green fluorescence decreased to 50% or less
after 70 hours under the condition of a temperature of 60.degree.
C. and 90% RH (FIG. 8).
As seen from the above-mentioned examples, the compound of the
present invention has a smaller half-width compared to existing
compounds, and may be used in the preparation of a color conversion
film having enhanced light stability.
REFERENCE NUMERAL
101: Side-Chain Type Light Source
102: Reflective Plate
103: Light Guide Plate
104: Reflective Layer
105: Color Conversion Film
106: Light Dispersion Pattern
* * * * *